Sex with strangers. Drug abuse. Mental illness. Among educated twentysomethings reared in the therapy culture, every personal scandal is fair game at the dinner table. Except for one: coming from money.

"Please don't tell anyone about my trust fund, I really don't want that information being passed around," one young New Yorker e-mailed me. "Oh, so I'm the bad guy?" another heir asked warily.

It may sound strange that in the most affluent society in the world, in the richest city in the world, Richie Riches would be ashamed of their inherited fortunes. After all, President Bush repealed the estate tax just for them, the luckiest 2 percent of the population!

But America still sees itself as an egalitarian society, and wealth is still a loaded issue. Those who bear the dreaded "trustafarian" tag say they have problems with guilt, embarrassment, and most importantly, figuring out what to do with their lives.

Thomas (not his real name), 25, grew up with a live-in housekeeper in a stately five-bedroom apartment in Brooklyn Heights. His father is a trust and estate lawyer in private practice; his mother retired as a partner in an investment firm. "She worked incredibly hard for 15 years and came away with a very nice nest egg from the boom years of the banking industry," he says. Thomas is candid about the effect of money on his own ambition. He returned home from his New England college a year early, finishing up his degree just this past semester at Columbia. He lived at home for a while, working for Howard Dean's campaign (mostly unpaid) and then selling outdoor advertising.

"I think relying on a future fund is dangerous," he says. "I spent one and a half years starting careers in two industries, politics and sales, that weren't for me. The time has gone by the wayside without me finding out what I do want to do." Now, Thomas works part-time at his father's law firm, just enough to make rent, while applying for new jobshe's currently interviewing at Showtime. His folks are getting a bit impatient. "My parents made their own money. For them it's emotionally nice that they can help me, but I think the flip side of that coin, there's a real fear that a hunger has been removed from the equation with my sister and I. At this age for me there's an emotional health factor in . . . going to a job and getting a paycheck."

The fact is, the very wealthy are not the only young adults who count on a little something extra from Mom or Dad. The baby boomers have emerged as one of the most prosperous American generations ever, even as their adult offspring's dependence has been lengthened by the necessity of getting several years of education for the contemporary job marketnot to mention a dearth of well-paying jobs with benefits.

The Research Network on Transitions to Adulthood, which studies the phenomenon of "emerging adulthood," found that parents provide $38,000 cash, on average, to their kids in years between age 18 and 34, a big increase over previous decades. In a way, we're all trust fund babies.

In the past generation, the increasing polarization of American incomes has created a new class: the super-rich. The number of households worth over $1 million nearly doubled between the early 1980s and the late 1990s. In 2003 two economists at the Boston College Social Welfare Research Institute reconfirmed their 1999 prediction that an astonishing $41 trillion of personal wealth,
including assets like real estate, will be bequeathed from one generation to the next over the next 55 years.

Even as lobbyists are now pushing for the estate-tax repeal to be extended past its current sunset of 2010, the financial services industry is preparing for what it calls the "wealth transfer phenomenon." In March 2005, The Wall Street Journal reported on the new "wealth education" programs sponsored by banks like J.P. Morgan and private financial management firms. These workshops, which can cost up to $150,000 per family, are designed to teach children, teens, and young adults the basics of investing and money management.

Just as the average boomer offspring is struggling to make a living, the children of the brightest new American success stories can't be blamed for feeling a little inadequate when comparing their parents' achievements with their own. Thomas's mother is well-known as a pioneering woman in the financial industry. Andrew (not his real name) is the son of a hedge fund manager who "struck gold" in the '87 stock market crash. His father grew up poor, attended Harvard on scholarship, and was "struggling" until the 1980s, living in his mother-in-law's basement. Now he possesses a $100 million fortune. Andrew was raised in Europe and lives in New York, drawing on his trust fund to try to get an American-Italian media business off the ground. Just a week ago, he accepted a job at a film production company in Rome.

Tyler, 21, has a similar story. "I would venture to describe my parents as archetypal New Yorkers," he says in an e-mail from London. His father, who made millions in investment banking, grew up middle-class and worked his way through college doing construction. His mother, born into a working-class family in Anniston, Alabama, came to New York as a Wilhelmina model.

Tyler, meanwhile, has enjoyed every possible advantage. He is an heir of a different mold: not the businessman but the bohemian. He attended prep school at Phillips Academy (Andover), went to Yale, and took this past year off to live in Europe. There he interned at galleries and film festivals and made a short film. He's staying on in London for the summer, working without pay for artists and at an art gallery and doing his own artwork. His parents have underwritten the whole enterprise, which Tyler calls "incredibly selfless" but also a source of anxiety. "The knowledge that there are financial buffers in my life makes me at times feel powerless," he says.

Barbara Blouin knows that feeling well. A trust fund recipient herself, she co-founded the Inheritance Project in 1992 to spread the word, through self-published books and pamphlets, about the baggage that comes with inheriting wealth at a young age. "Not having to work is a problem," she says, "because people don't get their feet on the ground and they don't have a sense of confidence. They feel dependent. Another problem is being different from their peers. They often refer to it as being 'in the closet.' It can be as embarrassing as that. There are other things that go with that. They may be more likely to have an addiction. They probably have a fair amount of shame or embarrassment and often guilt."

Blouin, however, says guilt is a danger only for those with a conscience and a sense of proportionprobably not the Paris Hiltons of the world. "Somebody who's quite happy having lots of money and stuff, who doesn't care that others may not, they might not feel guilty. But if they do care about those things they're almost certainly going to feel guilty."

For the scions who spoke to the Voice, free-flowing funds can cause social problems, but few of the materially blessed would confess to outright feelings of guilt. "I used to be very embarrassed of my privileges," says Andrew. "In Europe people would ask how I could be living there; I'd always say that my papa was with the diplomatic corps." Today, he is more honest but still doesn't "advertise" his riches. "Some people do treat me differently when they learn I have money. Doesn't really matter, I guess. It's not like I'll be buying drinks for everyone!" He shares a $1,400-a-month apartment in the Columbia Waterfront district in Brooklyn with a girlfriend who has a pile of student loans and no gilded background. "She refuses my helpI doubt my parents would let me pay off her college debts anyway."

Tyler says he, too, doesn't flash his cash around. He says that some unrestrained spending back in boarding school "took a toll on his friendships," when he was "unempathetic" and "unthinking" about the material differences between him and friends on scholarship.

Thomas allows that people have made derogatory comments about his family money over the years. Today, he says, a relatively modest lifestyle helps deflect criticism. "I can't really remember the last time I got angry or nervous or embarrassed. It's not as if I'm going to Suede and getting a banquette with three bottles of Crissy. I hang out on Smith Street and drink Red Stripes."

Generosity helps smooth the way with friends of more modest means. "I definitely know among my friends I'm not thought of as cheap," he says. "I know it'll all even out if I pick up dinner. And I've always been known among my friends for having people over. There's beer in the fridge, we'll have a barbecue and use my parents' apartment."

The peers at Thomas's tony Northeast college posed a somewhat different social problem: the clash between the haves and the have-even-mores. "In college some people really did have full staffs. I was a kid from Brooklyn who didn't wear Lacoste or drive a sports car. It was just assumed that I came from a blue-collar background and I might be on financial aid. I didn't jump to correct anybody." One night at dinner, someone reached to pay his check. "Assumptions were made. And I let them do it because they did share their bank account with their parents who were obnoxiously wealthy."

When these kids talk about class, they generally refer not to social divisions like family names but to material status markers like restaurant meals, clothes, cars, exotic vacations. Young people at various levels of relative affluencethose lucky enough to pay for private universities by check, for example, or live in the city without worrying about the rentlearn to navigate this world of luxe so smoothly that class distinctions seem to disappear. Yet bring up the topic of money directly, and the hidden boundaries are soon revealed.

In the end, though, the silver-spoon set is not so different from the rest of us. While they may not have to worry about basic needs, they eventually learn that the real challenge in life is making something of yourself no matter what you start out with. Thomas calls this attitude "a sense of luck of the draw, and hard work somewhere down the line." Andrew agrees. "I have many friends in the U.S. and abroad who are living off inheritances and aren't working, and some are very miserable," he says. "I tell them all that the remedy is to get a job and fend for yourself; it helps you find direction in life."